The Arsenal stalwart made 584 appearances for Arsenal during a 13-year spell at the club, a staggering achievement which can only be beaten by four other players in Arsenal's history.
He played an instrumental part in the early days of Le Professeur, and his support of the Frenchman has been largely unchanged. Which considering the mutual respect between the two is not surprising.
Speaking to talkSPORT over what the FA Cup could mean to both Arsenal and Wenger, he looked at the bigger picture and suggested it should be used as a springboard to propel them to the Premier League title next season.
'I think it would be fantastic if they can win that trophy [the FA cup] because then it will give them [the players] the sense of feeling of what it is like to win something with Arsenal football club,' said Winterburn.
'Then you can go on to try and achieve the bigger picture, which is obviously trying to win the league title for Arsenal.
'We can't say anything about the Champions League because we don't know whether they're going to be in it or not, but get the first trophy, and get that feeling.'
The defender went on to attack Wenger's transfer policy begging him to change it in the summer, that is, if he does stay on as Gunners manager: 'I also believe Arsene Wenger is going to have to change his transfer policy, if he stays.
'He has got to go into that market and really strengthen this team, because they've really struggled with the big boys.'
The point about Arsenal's recent record against the top Premier League clubs is one that is alarming to most Arsenal fans, and it is something Arsene Wenger does need to address as soon as possible.
Arsene Wengers record vs Top 4 teams in last 5 seasons. pic.twitter.com/Rd5gMTgaSW— EPL News update (@CFCtransferlive) March 25, 2014
The statistics speak for themselves, however, the summer transfer window did produce the Mesut Ozil signing. The signing of Ozil shouldn't be over-looked as it was, aside from Torres to Chelsea, the most expensive transfer in Premier League history.
A player considered by most, at the time, as one of the best in the world. Although, it soon became apparent that to see the best of Ozil, an intelligent, world class striker was needed - something Arsenal currently lack.
Hopefully, the summer transfer window will provide the final couple of pieces of the jigsaw and put Arsenal firmly back amongst, not only the best in the Premier League, but the best in the world.